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Holiday Homes in Ashland

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Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Ashland holiday homes

Smart TV, fireplace

Cozy Waterfall Oasis + Firepit

Cozy Waterfall Oasis + Firepit
East Durham
9.4 out of 10, Exceptional, (16 reviews)
"Everything was perfect!"
United States
Jen C.
The price is NZ$558
includes taxes & fees
8 July - 9 July
Cozy Waterfall Oasis + Firepit
Property grounds

Brand New 2 Bdr. Townhome Minutes from Windham Mtn

Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Hensonville
10.0 out of 10, Exceptional, (10 reviews)
"This is a very cute, very clean condo near Windham. Perfect for our family of 4. Would definitely stay again. "
United States
Kimberly K.
The price is NZ$647
includes taxes & fees
8 July - 9 July
Brand New 2 Bdr. Townhome Minutes from Windham Mtn
Smart TV, books, stereo, computer monitors

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!

Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Hunter
9.8 out of 10, Exceptional, (18 reviews)
"Nice home, spacious, and conveniently located minutes from Hunter. I would stay here again. "
United States
Jim D.
The price is NZ$766
includes taxes & fees
8 July - 9 July
Upgraded! Perfect location seconds from Hunter Mtn! Incredible views! King bed!
Exterior

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (61 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is NZ$383
includes taxes & fees
3 Aug - 4 Aug
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Smart TV, fireplace

Fox Hollow at Carter Bridge Estate

Fox Hollow at Carter Bridge Estate
East Durham
10.0 out of 10, Exceptional, (2 reviews)
"The unit was extremely clean,nice, everything we needed for a great time it was well stocked with all you needed close to town. Getting in touch with checking in was as easy as it could be. I would definitely visi again. Than you"
United States
Matthew E.
The price is NZ$1,447
includes taxes & fees
14 July - 15 July
Fox Hollow at Carter Bridge Estate
Fridge, microwave, oven, stovetop

2-bedroom in Peaceful Middleburgh Vroman’s Nose View

2-bedroom in Peaceful Middleburgh Vroman’s Nose View
Middleburgh
10.0 out of 10, Exceptional, (3 reviews)
"Janelle was very welcoming and accommodating. The house was decorated for the holidays and very clean, comfy, and cozy. There are wonderful amenities such as pool, fire pit, grilling area, if the weather allows for outdoor activities. "
United States
Lisa C.
The price is NZ$673
includes taxes & fees
28 July - 29 July
2-bedroom in Peaceful Middleburgh Vroman’s Nose View
Exterior

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is NZ$1,067
includes taxes & fees
8 July - 9 July
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Interior

Designer Private Catskills House + Fire Pit

Designer Private Catskills House + Fire Pit
Round Top
The price is NZ$940
includes taxes & fees
8 July - 9 July
Designer Private Catskills House + Fire Pit
Property grounds

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills

Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Gilboa
The price is NZ$425
includes taxes & fees
8 July - 9 July
Starlit Geodesic Dome Haven Overlooking a Mountain River in New York’s Catskills
Exterior

Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is NZ$917
includes taxes & fees
13 July - 14 July
Pines Vignette • Modern 3BR Home in Windham
Interior

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit

Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Durham
10.0 out of 10, Exceptional, (3 reviews)
"Was close to where we were attending a wedding and big enough to house us all!"
United States
Paul m.
The price is NZ$855
includes taxes & fees
20 July - 21 July
Mountain retreat/Hot Tub/Ski/Hike/Water Park/WIFI/Fire Pit
Exterior

Cozy Country Farmhouse Along the Catskill Scenic Trail

Cozy Country Farmhouse Along the Catskill Scenic Trail
Hobart
10.0 out of 10, Exceptional, (128 reviews)
"We loved our stay. The house was clean and generously stocked."
United States
Amy W.
The price is NZ$587
includes taxes & fees
20 July - 21 July
Cozy Country Farmhouse Along the Catskill Scenic Trail
Interior

Midnight Fox

Midnight Fox
Hunter
10.0 out of 10, Exceptional, (12 reviews)
"House was very clean and beds were super comfy after a day of skiing ! "
United States
Caroline I.
The price is NZ$756
includes taxes & fees
14 July - 15 July
Midnight Fox
2 bedrooms, free WiFi, bed sheets

Luxury Tiny Home Ski Cabin with Barrel Sauna Room!

Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Arkville
9.8 out of 10, Exceptional, (27 reviews)
"We are so happy we had a peaceful and relax time we love the sauna what a great place "
United States
Christian
The price is NZ$887
includes taxes & fees
14 July - 15 July
Luxury Tiny Home Ski Cabin with Barrel Sauna Room!
Property grounds

The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits

The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits
Phoenicia
The Bend: Trout Lily Suite • Pool • Sauna • Fire Pits
Interior

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter

Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Tannersville
10.0 out of 10, Exceptional, (4 reviews)
"The property is located on incredible Landfield....the view is spectacular and everything around is nature."
United States
NANCY
The price is NZ$1,295
includes taxes & fees
14 July - 15 July
Spacious 5 BR w/Mountaintop Views-2 Min to Hunter
Property grounds

Whimsical Dome Escape Amid the Majestic Mountains and Enchanting Rivers of New York

Whimsical Dome Escape Amid the Majestic Mountains and Enchanting Rivers of New York
Gilboa
The price is NZ$425
includes taxes & fees
8 July - 9 July
Whimsical Dome Escape Amid the Majestic Mountains and Enchanting Rivers of New York
Smart TV

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking

Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Catskill
10.0 out of 10, Exceptional, (1 review)
"Very clean; loved the spacious living room/kitchen/ dining area. Hope to stay here again. "
United States
Anonymous traveller
The price is NZ$796
includes taxes & fees
8 July - 9 July
Spacious 3BR Home ~ Sleeps 6 ~ Near Catskill Mountains & Skiing ~ Yard ~ Parking
Outdoor spa tub

Pond House at Carter Bridge Estate

Pond House at Carter Bridge Estate
Freehold
10.0 out of 10, Exceptional, (2 reviews)
"Property was great good times "
United States
Chris F.
The price is NZ$2,283
includes taxes & fees
13 July - 14 July
Pond House at Carter Bridge Estate
Interior

Great Lodge at Carter Bridge Estate

Great Lodge at Carter Bridge Estate
East Durham
10.0 out of 10, Exceptional, (2 reviews)
"My family and I spent a weekend here to celebrate my birthday which was soon after my dad passed away. A much needed peaceful and bonding few days in this beautiful home. From start to finish our stay was wonderful. Jarrett was communicative throughout if I had any questions. The accomodations were excellent and such a grand living space where no one felt crowded. My husband and I were actually inspired to buy a new mattress after the blissful sleep we had! Deer and turkeys roaming, quiet...
United States
Sabrina C.
Great Lodge at Carter Bridge Estate
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Ashland Hotel Reviews

Eastwind Windham

Eastwind Windham

10/10 Excellent
"Great!"
Andrew 3-night trip
Posted less than an hour ago
Eastwind Windham

Find out more about Ashland

Ashland Holiday Homes information

Number of reviews
230
Accommodation
553 Holiday Homes
Lowest Price
NZ$383
Highest Price
NZ$2,283